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EC number: 262-110-7 | CAS number: 60223-95-2
Dissociation constant
Administrative data
- Endpoint:
- dissociation constant
- Type of information:
- (Q)SAR
- Adequacy of study:
- key study
- Study period:
- April 17 to April 18 2013
- Reliability:
- 2 (reliable with restrictions)
- Justification for type of information:
- QSAR prediction: migrated from IUCLID 5.6
Data source
Reference
- Reference Type:
- other: QSAR report
- Title:
- Unnamed
- Year:
- 2 015
- Report date:
- 2015
Materials and methods
Test guideline
- Qualifier:
- no guideline available
- Principles of method if other than guideline:
- In SPARC, molecular structures are broken into functional units called the reaction center and the perturber in order to estimate pKa in water. The reaction center, C, is the smallest subunit that has the potential to ionize and lose a proton to a solvent. The perturber, P, is the molecular structure appended to the reaction center, C. The pKa of the reaction center is adjusted for the molecule in question using the mechanistic perturbation models. The pKa for a molecule of interest is expressed in terms of the contributions of both P and C.
pKa = (pKa)c + δp(pKa)c
where (pKa)c describes the ionization behavior of the reaction center, and δp(pKa)c is the change in ionization behavior brought about by the perturber structure.
The SPARC pKa calculator was trained on 2500 organic molecules, then validated on 4338 pKa’s (4550 including carbon acid) in water. The calculator was tested for multiple ionization’s up to the 6th (simple organic molecules) and 8th (azo dyes) for molecules with multiple ionization sites. In addition, the pKa models were tested on all the literature values we found for zwitterionic constants (12 data points), the thermodynamic microscopic ionization constants, pki, of molecules with multiple ionization sites (120 measurement data points, the RMS deviation error is 0.5), the corresponding complex speciation as a function of pH and the isoelectric points (29 measurement data points) in water. The diversity and complexity of the molecules used was varied over a wide range in order to develop more robust models during the last few years. Hence, the SPARC pKa models are now very robust and highly tested against almost all the available experimental literature data. - GLP compliance:
- no
Test material
- Reference substance name:
- Dinonylnaphthalenedisulphonic acid
- EC Number:
- 262-110-7
- EC Name:
- Dinonylnaphthalenedisulphonic acid
- Cas Number:
- 60223-95-2
- Molecular formula:
- C28 H44 O6 S2
- IUPAC Name:
- dinonylnaphthalenedisulphonic acid
- Test material form:
- solid
Constituent 1
Results and discussion
- Dissociating properties:
- yes
Dissociation constantopen allclose all
- No.:
- #1
- pKa:
- ca. 0.56
- Temp.:
- 20 °C
- No.:
- #2
- pKa:
- ca. 0.61
- Temp.:
- 20 °C
- No.:
- #3
- pKa:
- ca. 0.29
- Temp.:
- 20 °C
- Remarks on result:
- other: macro pKa
- No.:
- #4
- pKa:
- ca. 0.89
- Temp.:
- 20 °C
- Remarks on result:
- other: macro pKa
Any other information on results incl. tables
Species 1 diacid; Species 2 first monoacid; Species 3 fully dissociated form; Species 4 sec mono acid
pH |
Species 1 |
Species 2 |
Species 3 |
Species 4 |
Charge |
0 |
0,738 |
0,128 |
0,02 |
0,114 |
-0,281 |
0,2 |
0,63 |
0,173 |
0,042 |
0,154 |
-0,412 |
0,4 |
0,502 |
0,219 |
0,084 |
0,195 |
-0,582 |
0,6 |
0,367 |
0,253 |
0,155 |
0,225 |
-0,788 |
0,8 |
0,242 |
0,265 |
0,257 |
0,236 |
-1,015 |
1 |
0,144 |
0,25 |
0,384 |
0,222 |
-1,24 |
1,2 |
0,078 |
0,213 |
0,519 |
0,19 |
-1,442 |
1,4 |
0,038 |
0,167 |
0,645 |
0,149 |
-1,607 |
1,6 |
0,018 |
0,123 |
0,75 |
0,109 |
-1,732 |
1,8 |
0,008 |
0,086 |
0,83 |
0,076 |
-1,822 |
2 |
0,003 |
0,058 |
0,887 |
0,051 |
-1,884 |
2,2 |
0,001 |
0,038 |
0,927 |
0,034 |
-1,925 |
2,4 |
0,001 |
0,025 |
0,953 |
0,022 |
-1,952 |
2,6 |
0 |
0,016 |
0,97 |
0,014 |
-1,97 |
2,8 |
0 |
0,01 |
0,981 |
0,009 |
-1,981 |
3 |
0 |
0,006 |
0,988 |
0,006 |
-1,988 |
3,2 |
0 |
0,004 |
0,992 |
0,004 |
-1,992 |
3,4 |
0 |
0,003 |
0,995 |
0,002 |
-1,995 |
3,6 |
0 |
0,002 |
0,997 |
0,001 |
-1,997 |
3,8 |
0 |
0,001 |
0,998 |
0,001 |
-1,998 |
4 |
0 |
0,001 |
0,999 |
0,001 |
-1,999 |
4,2 |
0 |
0 |
0,999 |
0 |
-1,999 |
4,4 |
0 |
0 |
1 |
0 |
-2 |
4,6 |
0 |
0 |
1 |
0 |
-2 |
4,8 |
0 |
0 |
1 |
0 |
-2 |
5 |
0 |
0 |
1 |
0 |
-2 |
5,2 |
0 |
0 |
1 |
0 |
-2 |
5,4 |
0 |
0 |
1 |
0 |
-2 |
5,6 |
0 |
0 |
1 |
0 |
-2 |
5,8 |
0 |
0 |
1 |
0 |
-2 |
6 |
0 |
0 |
1 |
0 |
-2 |
6,2 |
0 |
0 |
1 |
0 |
-2 |
6,4 |
0 |
0 |
1 |
0 |
-2 |
6,6 |
0 |
0 |
1 |
0 |
-2 |
6,8 |
0 |
0 |
1 |
0 |
-2 |
7 |
0 |
0 |
1 |
0 |
-2 |
7,2 |
0 |
0 |
1 |
0 |
-2 |
7,4 |
0 |
0 |
1 |
0 |
-2 |
7,6 |
0 |
0 |
1 |
0 |
-2 |
7,8 |
0 |
0 |
1 |
0 |
-2 |
8 |
0 |
0 |
1 |
0 |
-2 |
8,2 |
0 |
0 |
1 |
0 |
-2 |
8,4 |
0 |
0 |
1 |
0 |
-2 |
8,6 |
0 |
0 |
1 |
0 |
-2 |
8,8 |
0 |
0 |
1 |
0 |
-2 |
9 |
0 |
0 |
1 |
0 |
-2 |
9,2 |
0 |
0 |
1 |
0 |
-2 |
9,4 |
0 |
0 |
1 |
0 |
-2 |
9,6 |
0 |
0 |
1 |
0 |
-2 |
9,8 |
0 |
0 |
1 |
0 |
-2 |
10 |
0 |
0 |
1 |
0 |
-2 |
10,2 |
0 |
0 |
1 |
0 |
-2 |
10,4 |
0 |
0 |
1 |
0 |
-2 |
10,6 |
0 |
0 |
1 |
0 |
-2 |
10,8 |
0 |
0 |
1 |
0 |
-2 |
11 |
0 |
0 |
1 |
0 |
-2 |
11,2 |
0 |
0 |
1 |
0 |
-2 |
11,4 |
0 |
0 |
1 |
0 |
-2 |
11,6 |
0 |
0 |
1 |
0 |
-2 |
11,8 |
0 |
0 |
1 |
0 |
-2 |
12 |
0 |
0 |
1 |
0 |
-2 |
12,2 |
0 |
0 |
1 |
0 |
-2 |
12,4 |
0 |
0 |
1 |
0 |
-2 |
12,6 |
0 |
0 |
1 |
0 |
-2 |
12,8 |
0 |
0 |
1 |
0 |
-2 |
13 |
0 |
0 |
1 |
0 |
-2 |
13,2 |
0 |
0 |
1 |
0 |
-2 |
13,4 |
0 |
0 |
1 |
0 |
-2 |
13,6 |
0 |
0 |
1 |
0 |
-2 |
13,8 |
0 |
0 |
1 |
0 |
-2 |
14 |
0 |
0 |
1 |
0 |
-2 |
14,2 |
0 |
0 |
1 |
0 |
-2 |
Applicant's summary and conclusion
- Conclusions:
- The pKa for di C8-C10, branched, C9 rich, alkylnaphthalene disulfonic acid (DNNSA) is 0.29-0.86.
- Executive summary:
The dissociation of di C8-C10, branched, C9 rich, alkylnaphthalene sulfonic acid was evaluated with the SPARC model. This model, developed by the US EPA ( SPARC Automated Reasoning Calculator v5.1 ), has been validated in 2003 and has a high degree of accuracy. The substance DNNDSA is a strong acid and dissociation occurs at less than pH 1. The model calculated pKa is 0.29 -0.89.
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